Greg Isenberg is a multi-exit Silicon Valley entrepreneur and owner of Late Checkout product studio. He has:
- Headed Product Strategy at WeWork
- Been an advisor to Reddit
- Founded a startup, Islands, which was sold to WeWork
- Founded 5by, which was sold to StumbleUpon
Guest Author: Greg Isenberg
This is a story I’ve never shared with anyone… January 2nd, 2019. I was broke. I had raised $2M in VC for my startup, but the bank account was empty.
VCs had bailed.
“Facebook will copy you,” they said.
I was burning my savings to fund payroll. Desperate for an exit, I got a lead: an intro to an exec at TikTok. Let’s call her Sarah.
She seemed interested in buying the company. LFG.
Deals get done in person.
So, I said, “I’ll be in LA later this week.”
“Oh really? Yes, let’s meet,” she replied.
Boom. There was a chance.
I rented a Kia Soul—not a G-Wagon, but it would do. Hotel Tonight showed rooms at $500+, so I grabbed a Best Western in Pasadena, an hour from TikTok HQ but only $99/night.
I arrived at 8 PM, had a cheap buffet dinner, and went to bed thinking, “Tomorrow is the day.”
Next morning, I rushed to my Kia Soul and headed to the office.
“I’m Greg Isenberg from Islands, here for Sarah,” I told her EA.
“Have a seat right here.”
My meeting was at 9 AM.
9:05… 9:10… 9:25…
“Is she coming?” I wondered.
The EA approached. “Sarah can’t make it.”
I asked to reschedule.
“Sorry, we’ll get back to you.”
I literally felt my heart burst in real time. I felt terrible.
Time was ticking.
Defeated, I walked back to my bright green Kia Soul with barely any gas.
I emailed her, staying positive, and left my number.
I got in the car, put it in drive, and headed north to San Francisco. Feeling defeated, I wondered what my girlfriend would think.
As I got onto the I-5, an unknown number called. I answered.
It was the TikTok exec. She apologized for missing the meeting and wanted to make a deal happen. “Can I intro you to the corp dev team?”
I never sold to TikTok, but it got the M&A process rolling. I ended up with a few offers and did well. I even joined TikTok as an advisor when I didn’t sell to them.
It all worked out. And my team did well too. From the exit, they bought houses in NYC and brand new cars (most nicer than a Kia soul tbh)
And I got my nest-egg back.
Why I’m sharing this:
1. Entrepreneurship is full of ups and downs. Here are a few lessons I learned:
2. Stay positive when the world feels like it’s crashing down. You never know what might happen.
3. Relying on VCs means you’re never truly in control. One moment you’re everyone’s darling, the next moment they leave you on read.
4. Shoot your shot. Always.
Startups aren’t all red roses and green cash, but they’re fun.
Now, I focus on profitable, cash-flowing businesses—running agencies, internet communities, and SaaS products. Less stress.
That startup experience aged me a decade.
But here’s the thing… you learn a lot about yourself and others through startups. I wouldn’t have changed a thing.
It’s a beautiful thing.
By the way, I put together 30+ profitable startup ideas that are pretty validated. You can grab them here totally free.
Grab ’em while you can…
https://lnkd.in/dGt8Cch4
